


the fate that befell me

by SebGray



Category: Critical Role (Web Series)
Genre: Alternate Universe - Modern Setting, Alternate Universe - Sugar Daddy, Blind Date, Cunnilingus, Doggy Style, Dom/sub, Explicit Sexual Content, First Dates, First Kiss, First Time, M/M, Oral Sex, Past Character Death, Past Relationship(s), Rough Sex, Safer Sex, Self-Esteem Issues, Trans Male Character, opposite of a slow burn
Language: English
Status: In-Progress
Published: 2020-04-16
Updated: 2020-04-15
Packaged: 2021-03-02 02:41:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,075
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23677822
Author URL: https://archiveofourown.org/users/SebGray/pseuds/SebGray
Summary: Two years after Vax died, Shaun Gilmore is still looking for someone. After far too many hollow dates to count, he ends up with Caleb Ermendrud, a grad student who isn't looking for much. They end up quickly finding a lot more than just a transaction.
Relationships: Shaun Gilmore/Caleb Widogast
Comments: 25
Kudos: 103





	the fate that befell me

**Author's Note:**

> new fic idea who this  
> seriously idk how i pumped this out but uh, hope y'all enjoy  
> (also idk how gilmore talks so uh, take this, it's probably Not Great)

Getting ready for dates had become a hollow routine now.

Shaun’s past few relationships had been less like romance and more like dull charity work. Write some checks, give some gifts, go out to a few dinners, maybe an event or two. Even the sex, while never _bad_ or forced or nonconsensual, was little more than a favor for the other person involved. As much a gift as his money. His longest relationship in the past two years had lasted three months, and his hope for the next one was barely pulsing. But Keyleth had insisted it was a good match, selecting his profile from the sea of eager sugar babies waiting for a nice, rich, handsome man to show up in their lives and fix their problems by throwing money at them. 

Two weeks before, she had sent the clumsy screenshot to him. Caleb E. He was handsome, for sure. Freckles, long red hair, glasses. Spring-sky blue eyes. He was mostly hiding his face, though, either cupping it in his hand, drinking coffee, sticking his nose in a book, making a goofy expression. 

_ Caleb Ermendrud. He’s from the Zemni Fields in Dwendali _ , she texted.  _ Engineering student. Going for his master’s. _

Shaun knew what that probably meant. Dealing with student loans would probably going to be on his list of needs. But the engineering was unique enough.  _ So he’s smart? _

_ Top of his class. Perfect GPA.  _

_ Any scholarship? _

_ Don’t think so? Can’t tell. He’s going to Emon University. Transferred from Soltryce Academy in Dwendali? I tried Googling him but I can’t find anything beyond his grad school stuff, though. Might be a name change thing, I think. I'm finding someone else with the same last name and a different first one, but I can't tell for sure. _

Shaun frowned at the screen. Concerning. He didn’t like to snoop too much, but he liked at least a bit of background. Make sure he wasn’t dealing with a con man or a criminal. 

_ Show me the rest of his profile. _

Letting Keyleth have control of his dating app had been...a journey, so far. After everything that happened, the two had become oddly close confidants, but so far all of her picks had been misses. Hollow dates who sucked up to him for his money. 

She sent the rest of his profile. He liked reading basically anything he could get his hands on, was fluent in multiple languages, wasn’t much for modern pop culture but liked classic movies and plays and ballets and old music. “But I really like science,” he wrote. “I do not like to talk very much but if you ask me about quantum physics or chemistry or anatomy or biology or engineering, I will not stop talking about it.” Not the _most_ generic, at least.

_ Anything else? _ he texted Keyleth. The last bit of the profile was his needs -- what Shaun was likely going to be paying for. Student debt, maybe textbooks, new laptops, rent, food. Some were more specific. 3D printers, cameras, clothes and shoes, cars even. 

But his list was surprisingly short. “I really just want to be able to afford to transition. I have no insurance and cannot afford it, and I cannot get more than a minimum wage job with my degree and experience. I am trans, and can barely afford therapy and medicine as it is. I do not mind not having anything else, no gifts or bills being paid or fancy dinners. Just HRT, potentially other surgeries.”

_ Trans. _ Shaun felt his posture wilt, remembering when he first saw Vax’s profile, asking for his transitioning over everything else, even housing and food. There weren’t many trans guys on this particular service, and Vax had been the first one he’d met. Seeing this...hit differently than with the other profiles Keyleth had shown him.

So they made the arrangements. Caleb’s texting was stiff, formal. Surprised. He hadn’t expected a response, much less actual plans. Shaun frowned. Some people tried to force fake humility but this wasn’t that. He authentically seemed to believe he wouldn’t interest anyone.

Shaun didn’t know what worried him more: that this would be different, or that this would be the same as everything else.

He picked his usual purple suit, with a nice floral button-down and gold jewelry. He hesitated as his hand traced over the silver ring on the simple chain, still set in the box where he’d put it after Vax’s funeral. He picked it up, examining the band with its raven feather,  _ do not go far from me _ engraved within in Shaun's slow handwriting. The ceremony in the hospital room wasn’t technically legal, but it was a wedding to them all the same. Gilmore still wore his own ring, though on his right finger now, and Keyleth wore hers and Vax’s other ring around her neck at all times. Gilmore meant to wear Vax’s as well, but never could. Even now, two years later, he could still hear Vax’s last breath, his face so skeletal in color and shape, and the drone of the heartbeat monitor once there was nothing left to track. But something told him to start now. He slipped the chain over his head, hiding it under his shirt and the other layers of jewelry. With a sigh and a final adjustment, Shaun stood straight and practiced his charming smile.

Time for the act.

* * *

Caleb fiddled with his shirt sleeves in the back of the Uber, regretting now that he had decided against wearing the too-big blazer. The man -- his date, his potential sugar daddy -- had told him not to look up the restaurant. Keep it a surprise. Just punch the address into the app. Given that the guy had sent him fifty dollars via Venmo for just the ride, Caleb was certain it must’ve been some fancy place that served hundred-dollar plates and bottles of wine worth more than Caleb’s bank account could ever eke out. And here he was, about to show up in his worn-out binder, his shirt that couldn’t decide on where it was going to lay second by second, and his work pants, still stained with powdered sugar.

_ This was a terrible idea. You can’t even accept  _ compliments _ , and now you are trying to convince some handsome rich man to spend more money on you than you have ever seen in your lifetime. How did you think this was going to end well? _

The driver pulled up to the place. “Alright, have a nice day ma’am.”

Caleb shrunk, muttering a thank you as he got out. On the sidewalk, he gave the driver five stars and a good tip despite the fact that he wanted to collapse and disappear like a tiny black hole. Once the car disappeared down the street, he turned and looked up at the place. It was actually...lovely. A cursive sign hanging above the door said  _ The Whitestone. _ It was a pretty, white-painted building with a vine-surrounded outdoor seating area. Inside, through the windows, he could see a dining room with white cloth-covered tables and shining silverware. It was filled with sunlight coming in from the huge windows. He shifted nervously, hands going up to maybe tie up his hair. Caleb caught his reflection in the glass. No wonder that driver called him ma’am. He needed a haircut if he wanted any chance of passing.  _ Not that that’d help much. Haircuts don’t help once people see your face or hear your voice. _

A car pulled up to the sidewalk behind him, and Caleb turned when he heard a hearty voice say, “I’ll text you when I need to be picked up, Sherri!” Sure enough, Shaun G. from the dating site was standing there, dark hair pulled back, tan skin warmed by his rich purple suit, wearing enough gold around his neck and on his fingers to pay for this semester’s tuition at least. Caleb froze, feeling small and unremarkable as an old garden gnome.

_ Try to be confident for once,  _ Caleb tried to tell himself.

The man smiled, and the handsome sight of him combined with the happy rhythm of his laugh made Caleb all the shakier. “You must be Caleb!” he greeted with a strong two-handed handshake. “My name is Shaun Gilmore. It is a  _ pleasure _ to meet you!”

A smile escaped Caleb as he managed to mutter, “ _ Ja, danke _ , it is nice to meet you, too.” But then his brain fully fizzled. _That_ was why he seemed so familiar. He was  _ the  _ Shaun Gilmore. Of Gilmore’s Glorious Goods. One of the richest men alive. And he happened to click yes on a random weird-looking grad student’s dumb dating profile.

Caleb’s dread went from looming to mountainous in moments.

“Was everything alright with the driver? Did you have any trouble?” Mister Gilmore cocked his head, concerned.

“Oh no, everything was fine,” Caleb stuttered, pulling his hand away and shoving them in his pockets.

“Was the money enough?”

Caleb nodded. “Far more than enough. Would you like me to send the rest back? The ride was only thirty dollars.”

“No, no, keep it! Least I could do!” Mister Gilmore opened the door. “After you, Mister Caleb.” His smile was wide but warm and true. Caleb’s dread briefly vanished in a puff, because the way the man had said his name felt like the greatest compliment. He felt his cheeks burn, then his eyes darted down as he muttered a thank you, heading into the restaurant.

The hostess, a pretty woman with neat brown hair and a sunshiny grin, grabbed some menus as soon as she saw them enter. “Good evening, Mister Gilmore. Glad to see you tonight.” She led them to a small table in the corner, next to a window. Here, Caleb saw that outside the restaurant was a huge garden, filled with flowers and vegetables and roaming butterflies, all turned rosy hues with the sunset. Mister Gilmore pulled out Caleb’s seat, making the blush return as he muttered  _ thank you _ .

As Mister Gilmore settled in his seat, the hostess began her spiel about specials before stopping. “Oh, sorry, did you want to do the chef’s special again?”

He looked over at Caleb, eyebrows raised. “Usually when I come here I like to be surprised. Otherwise, I’d order the same thing over and over again.” He laughed. “Would you be interested? They’ve never disappointed me.”

On the one hand, Caleb hated surprises. On the other hand, nothing about this evening so far had been predictable, and he worried that if he saw the prices on the menu, he might bolt. “Uh, sure.”

“Splendid!” Mister Gilmore laughed and turned to the hostess, handing over the menus, unopened. “As for the drinks, I would like champagne, if you wouldn’t mind.”

When the hostess nodded and turned to Caleb, he said, “Do you have coffee?”

“Yes. Hot or iced?”

“Hot. Black. No cream or sugar. _Danke._ ” Caleb forced a smile.

She grinned and nodded. “Of course. Thank you.” With the beaming grin, she hurried off.

Caleb tried to remember to breathe once she left them alone. “Thank you for inviting me,” he said.

“This pleasure is all mine, Mister Caleb.”  _ Gods, if he keeps on doing that, I am doomed. _

“You come here often?” This must be where he brings all his sugar babies.

“Yes, as often as I can, when I’m in Emon. I’ve been coming here since it re-opened, back when my store used to be right down the road.” He grinned. “I’ve brought damn near everyone I can to this place. The food is amazing, best in town by far.” He leaned in with a mischievous eye, whispering, “Except for the Trickfoot Diner. But don’t tell anyone here I said that.”

Caleb chuckled, fidgeting with his glasses. “I go there all the time. The one run by Pike?”

“Yes! Have you had their cherry pie?”

“ _ Ja _ . She usually sneaks me a slice when I come in to study.”

“It’s _divine_. I always try to sneak over when I can. She’s a longtime friend of mine.” Mister Gilmore grinned happily, but then the smile faded into something more...wistful. “She helped me through a lot,” he muttered, grin returning, though more forced, the crinkle in his eyes now gone. “Her food does wonders, really.”

Caleb nodded, humming a little, looking down at his pristine silverware wrapped in a perfect blue napkin. He remembered sobbing into Pike’s shoulder the night after he had gotten the call about Molly, then blubbering to her over a plate of food and a cup of tea that never went empty. He never really thought that someone understood that experience.

The hostess returned with a mug of warm coffee, two glasses, and a champagne bottle. She popped the cork off with practiced ease and asked, “Would you like a glass, sir?”

Caleb looked up, realizing she was talking to him. “Oh.” His eyes went to Mister Gilmore, who shrugged. “ _ Nein, danke _ ,” he muttered, arms pulling in as he held his coffee close, taking a long sip.

“Oh.” She cocked her head in surprise, setting down both glasses anyways as she poured only one, placing the bottle closer to Mister Gilmore. “Your food will be out as soon as possible.” Her grin returned as she left.

Caleb muttered more thank-yous as he eyed the champagne bottle. He didn’t recognize the brand name but...was 1985 a good year for champagne? He had no clue.

“So, tell me, Mister Caleb, what brought you to Emon? Not many Dwendalians come over here.” Mister Gilmore sipped the champagne, fingers moving gracefully around the small glass despite his hand's size.

“There were some issues at my old university,” Caleb mentioned, arms stiffening again. “I met a professor from Emon University when she was lecturing there, Professor Vysoren?”

“Oh, Allura! She’s fantastic.” Mister Gilmore grinned enough to light up his face.

“ _ Ja _ . She heard about what was going on and offered to get me a recommendation to Emon after everything settled. I ended up getting a good scholarship, too.” He smiled a little. “Now she is helping me with my thesis.”

“Oh? What is that about?”

Caleb shrugged. “It’s about designing better communication for emergency responders.” He looked down at his coffee, the desire to drink it now gone. “Someone close to me died because no one could find them.” He forced himself to take a sip. "The least I can do is to try to fix it.”

Mister Gilmore nodded slowly, his smile slipping off. Something in his gaze...shifted. Caleb could not fully place it His face had wilted like an old flower, eyes drifting to a loose thread in the tablecloth. “I can understand.” He hesitated, then took a deep breath and continued, “After my first partner died, I donated...a lot of money to the hospital that took care of him. And even more to cancer research. When someone close to you dies of something you know you can possibly prevent in the future...the least you can do is do what you can.” He smiled softly. “It’s admirable that you’re trying to properly change things. All I can do is throw money or merchandise at the problem.” He shrugged and took a drink.

“Funding is important," Caleb said. "A lot of the problems I have found with emergency responders is a lack of money or technology. Ride-sharing apps, delivery apps, and social media can track your location almost anywhere, down to the floor of a building, but a lot of emergency services do not have that. Because of this a lot of people die." His throat felt tight, almost like it was choking him from within. "Including someone I loved.” He shrugged. “I do not know if it will work, though. I still have to work it out.”

“Of course. But...I think you will. You seem like the type of person who can make things work out.” Gilmore smiled softly. “I wish you the best of luck, all the same.”

Caleb grinned a little. “ _ Danke _ .”

The first part of the meal came in. Chilled cucumber soup with chicken, squash, and light chili peppers. Caleb got a new serving of coffee, and he murmured his thanks. “Is this a multi-course meal?” he asked Mister Gilmore.

“Yes. Hope you don’t mind.” Mister Gilmore grinned as he picked up his spoon. 

“ _ Nein, _ of course.” Caleb smiled. It was probably going to be the most food he had eaten in a while. He tried the soup and it was...surprisingly good. A nice balance of sweet and salty, with a warm tingly spice settling at the back of his throat.

“Are you enjoying it?” Mister Gilmore asked with a grin.

“ _ Ja _ , it is very good.” Caleb noticed his bowl was almost empty and tried to go a bit slower. He didn’t want Mister Gilmore to think he was starving.

(Did consuming nothing but coffee for the last two days count as starving? He didn’t know and wasn’t about to ask.)

“You said you were interested in the sciences. Beyond that, what kind of things do you like?” Mister Gilmore asked once Caleb finished.

“I like reading a lot. Outside of my apartment, work, and class, I probably spend the most time at the university library, going through a stack of books.”

“What kind of books do you like?”

“Mostly nonfiction. History, linguistics, art.” He shrugged. “Not terribly interesting.”

“Oh, to the contrary,” retorted Mister Gilmore as he raised the spoon to his lips. “I think knowledge is more fascinating than you might think.”

The fire under Caleb’s skin returned. “What kind of books do you like?” he stammered.

“A good mix of things. I listen to audiobooks when I travel a lot. Mostly fiction. I love anything that will transport me to another place. A nice little escape from the real world. It’s what I call a vacation nowadays.” He laughed a little.

Caleb grinned a bit. “Someone like you does not take many breaks?”

Mister Gilmore shrugged. “I try to balance business with pleasure, but that usually doesn’t involve long vacations. My schedule is far too full of business meetings, charity events, and...dates with handsome men to make room for anything more than that.” With the last part, he gazed into Caleb with a strong stare, making his body feel like it was about to dissolve into the air.

“Does that make this a charity event?” Caleb laughed a little. Mister Gilmore’s smile dropped.

With quiet movements, Mister Gilmore took Caleb’s hand in both of his. He had not noticed how warm they were before. His gaze now was soft, his voice gentle and slow. “Caleb. Please do not feel the need to demean yourself. I wouldn’t be here if I didn't find you attractive.”

Caleb blinked, confused. “You are one of the wealthiest men in the world. You could have almost anyone you like. Why me?”

Mister Gilmore smiled softly, pausing for a moment. He took a breath in and said, “My wealth makes me an idea in the eyes of most people. You’re one of the few who sees me as a person. In the past few years, I haven’t met many people like that, especially people who want to enter this...” One hand let go as he seemed to look for the word. “...arrangement.” His smile widened as he added, “Besides, my wealth doesn’t change my preferences, and I  _ definitely _ think you’re attractive.”

Caleb forgot how to breathe for a minute. He wanted to curl up and hide, but he also wanted to never let go of Gilmore’s hand. The idea of this wealthy, charming, attractive man liking  _ him _ , of  _ all people, _ made no sense to him. He had seen the profiles of other people on that app. They were gorgeous. He was nothing.

Two thoughts spoke up.

_ You will never deserve this. Once he realizes that, he will throw you out, and you will be back where you started. Miserable and broke and desperate and alone. _

The other was quieter. But it made his chest feel like a helium balloon being released into the sky.

_ He likes you. Take this opportunity. When will you ever have it again? _

Caleb smiled and said, “Thank you.”

Gilmore smiled fully, eyes crinkling. Slowly, he brought Caleb’s hand to his lips and kissed it. “Thank  _ you _ ,” he said, and Caleb felt like he was going to melt.

* * *

The conversation continued between them, flowing from one topic to the next like a steady river, with the only way Shaun could tell time was passing being the changing of courses and the darkening of the sky through the window. 

As they finished the last of their penultimate course, a nice salad with crisp greens and a tart, sweet dressing, Caleb finally asked to try some champagne, and it made Shaun’s heart thunder in his chest to see his full grin. “I never thought champagne tasted good,” he said. “I have only had really cheap stuff on New Year’s.”

Shaun smiled as he raised his glass. “I hope you won’t mind having it more often.”

“Really?” He shrank again, examining the glass. “You will not mind spending that kind of money on me?”

With a sureness he hadn’t expected, Shaun nodded and said, “It would be my pleasure to spoil you.”

Caleb looked down. “What do you expect in return?”

Shaun shrugged. “Nothing you don’t want to give. I’d  _ like _ the honor of having your company. I have a schedule, but I am more than willing to shift things where I can to make time for you. Really, I do not expect you to do anything, romantic, sexual, or otherwise, that you do not want. My only request is that you respect my privacy as a man of my position. That is all.”

“So...do I have to sign a form or something? An...NDA? Is that the term?”

Shaun shook his head, setting down his glass. “Definitely not. No contracts, no rules. Nothing like that. It’s only my request to you, one that I fully intend to keep in return. I will not share the private things you share with me, and I simply ask that you do the same.”

Caleb nodded. “Of course.” He hesitated, then took another sip of champagne. “Well...what do you  _ want _ to do?”

“Again, whatever you are comfortable with. I am more than able to take care of myself. However, my typical pattern is providing my partner with money to pay for their needs, gifts they want or that I think they’d enjoy. Beyond that, I like taking my partner out on dates. Dinners like this, or maybe trips to museums. Once I have spent a good amount of time with them, they might accompany me to various events, come with me on work trips, come to my home to have dinner, meet my other friends. But that, of course, is completely up to you. I am willing to go at your pace.”

There was another moment of hesitation, of thought, before Caleb finished his glass. “I think...I’d like to do that. But...would we be a couple?”

“I do not expect you to be exclusive,” Shaun said. “My longest lasting partner had a girlfriend when we first began our arrangement, and they stayed together for as long as we did.” Avoiding the full details felt like politely directing attention away from a gaping wound, but going any further felt too fast. “I, however, tend to be monogamous. I only have one partner at a time, and though I have plenty of friends and might flirt in good fun, I do not seek relationships beyond that. Again, I do not have that expectation for you.”

“That was not  _ entirely _ what I meant,” Caleb said, nodding, “but it is good to know. I meant to say...would we be lovers?”

“Sex does not have to a part of the relationship if you don’t want it.” Shaun felt his body turn warm as he leaned in. “However, if you would  _ like _ sex, I will only say no if we are in a situation where we can’t be sexual or can’t enthusiastically consent.”

Caleb’s cheeks once more turned red, the blush reached the tips of his ears. He brushed a strand of hair behind one of them and murmured, “That was not  _ entirely _ what I meant either, but...that is also good to know.”

Shaun grinned and chuckled softly, relieved to see Caleb return with a smile.

“Would we be...romantically involved?” Caleb fiddled with his glasses, then his shirt. His voice was tight and quiet. “Because you use the word  _ partner _ instead of sugar baby or whatever the term is, but you also call this an  _ arrangement  _ and I want to be sure. Because I am also fairly monogamous, and while I am not terribly experienced with sex, I would like to do it with you, because you are very handsome and kind and I feel like I can trust you, but...are we dating? Is this a transaction or a relationship?”

Shaun sighed. “Ah. I apologize for the confusion. I typically mean  _ partner _ in the business sense, but...for you, I would like to potentially make an exception, if you don’t mind?” Shaun realized he had never been this nervous since his first date with Vax, once he had realized he wanted something more than a simple transaction.

Caleb took in a sharp, shallow breath. After a pause, he nodded. “I think I would like that. I am sorry if I am not very experienced or impressive--”

Shaun took Caleb’s hand again. “Do not apologize. You are more than enough for me.”

Caleb smiled softly. “Thank you.”

Dessert came. One slice of chocolate cake with glazed strawberries and a coffee-chocolate frosting, and two forks. “I am so sorry, but we ran out of this dessert and this is all we have--”

“It is fine,” Caleb said. “I do not eat many sweet things anyway. We can share.”

She nodded. “Of course. Enjoy.” With a smile, she hurried off.

Shaun handed him one of the forks. “Their desserts are always my favorite part.”

“I will try some,” Caleb said, a graceful hand taking the fork. “I do not have much of a sweet tooth, I am afraid.”

“Take what you want,  _ my dear _ ,” Shaun said, adding the Marquesian nickname as a matter of habit. “Oh! Forgive me.” His face felt hot and his perfectly tailored suit suddenly felt stuffy.

“Was that Marquesian?” Caleb asked, head tilted.

Shaun nodded. “Yes, that was where I was born and raised. A small town outside of Ank’harel. My parents still live there.”

“Ah. I studied some Marquesian at my previous school.” He chuckled, taking a bit of the cake from the slice. “I stopped in favor of more engineering courses, but it was a really good class. Lovely professor. I tried studying it a bit more from the Emon University library, but I cannot really speak it yet. Reading about it in a book can only do so much, _ja?”_

“Really? I’d love to teach you.” Shaun felt giddy with the idea. “I'm unfortunately a bit rusty. I only use it nowadays when I speak to my parents.”

“I would be happy to help you practice,” Caleb said, taking a bite with his rare full grin. He moaned a little with the flavor. “I did not expect coffee and strawberries to pair so well.”

“It is one of their more popular desserts for a reason,” Shaun said, his heart returning to roar in his ears. “I am glad you enjoy it.”

The dessert was gone quickly, leaving only traces of frosting and crumbs once the bill arrived. Shaun stuck his card in the holder, careful not to show Caleb the price.

“I hope it was not too expensive,” he muttered.

“It was worth every penny,” Shaun said. He opened a part of his wallet, a metal folding thing made by Vax’s brother-in-law for their wedding gift, and pulled out a folded up one hundred dollar bill, tucking it discreetly under the saucer of Caleb’s coffee mug. Caleb’s eyes followed his hands as he did so.

“You tip that much everywhere you go?” he said with a small laugh.

“I try to. If I’m at a place with a tip jar I try to divide it into smaller bills so it’s less likely to be stolen and easier to split.” The hostess returned with the check, which Shaun signed, including an additional tip to even out the charge. He returned his card to his wallet and closed it with a small click.

“Thank you both for coming tonight,” she said, grinning. “And also, Mister Gilmore? The owner is here. I haven’t told her you’re here yet. Would you like me to?”

“Oh, Vex!” Shaun grinned. Vax’s twin sister was still a dear friend of his. “Of course! I haven’t seen her in far too long.”

“Alright. I’ll let her know right away.”

Shaun turned to Caleb. “The owner of this place, Vex’ahlia de Rolo, is an old friend. I hope you don’t mind meeting her?”

Caleb shook his head. “No, of course not. Would you...what would you be introducing me as?”

“My partner,” Shaun said, quickly adding, “She knows what that means.”

“Oh. Okay.” Caleb nodded, getting tense again. Shaun’s chest clenched with worry for a moment.

Vex hurried over, wearing her typical fine green dress, fancy coat, and proud posture. Shaun stood, Caleb quickly following as she gave Shaun a tight hug. “Gilmore, I have not seen you in far too long!’ She poked him with a pristinely painted nail with each of those last three words. “You need to tell me when you come! How else am I supposed to scare off the riffraff from you?”

“Careful, Vex, I think I’d prefer to keep this one,” Shaun said with a laugh, gesturing with his head towards Caleb. “This is Caleb. He’s studying at Emon U under Allura.”

“Oh, did Kiki finally find you a good one?” Vex laughed, a clear and musical sound, as she turned to shake Caleb’s hand. The poor man was blushing from his ears to his collarbone. “I am Vex’ahlia de Rolo. One of Gilmore’s old friends from when his company was first starting up.”

“Caleb Ermendrud,” Caleb muttered. 

Vex looked Caleb up and down and said, “Yep, not riffraff. I’m guessing you’re about to head home?”

“Well, we just finished.” Shaun looked over to Caleb, who didn’t say anything. 

“In that case, I’ll see you two out. I only stopped by to check up on everything. And...” She examined the table, finally picking up the mug and saucer and looking underneath it. “Yep, I don’t have to kill you.” Caleb chuckled, and Vex said to Shaun, “You were right.” She returned them to their original position. “I’ll let Cass know where you hid it.”

Shaun slowly wrapped an arm around Caleb, giving him time to pull away. He did not. Vex led them out the door, and she and Shaun chatted idly about Percy, the kids, Trinket. He only really paid attention to Caleb’s warm press against him as he relaxed.

The night air was bitingly cold, and Shaun felt Caleb tense next to him. Vex waved goodbye, quickly heading back inside. Once she was gone, Shaun took his phone from his pocket and took off his coat, pulling away just long enough to drape it over Caleb's shoulders. He started to object, but Shaun interrupted, “I run warm enough to survive a little chill, Caleb.” He nodded, pulling the jacket tight around him. “Would you like to drive home with me, or get an Uber? I’ll stay with you until the car comes.”

Caleb muttered, “I did not think the plan was to go home.”

Shaun’s eyebrows rose. “Would you...like to stay the night? I have a spare bedroom.”

“I do not have to,” Caleb said.

“You do not,” Shaun said. He smiled, placing a hand on Caleb’s shoulder. “But I’d like you to if you wish.”

Caleb paused. In the dimness of the street, Shaun could still see his blush return. Very quietly, so soft Shaun could barely hear, Caleb asked, “Would I  _ have _ to sleep in the spare room?”

Shaun smiled, feeling like a nervous teenager when he first snuck a boy home. “If you don’t want to, my bed has plenty of space for the two of us.”

Caleb once again moved closer to Shaun. “I would like that,” he said, grinning wide once again. Shaun felt himself floating every time he saw Caleb genuinely smile.  _ Gods give me mercy, I want to see that for all of eternity. _

“Alright. Shall we stop at your place to get whatever you need? Change of clothes, toothbrush?”

“ _ Ja _ , if you do not mind,” Caleb said. “I can give you the address?”

“Of course.” Shaun texted Sherri,  _ He is staying with me tonight. We’ll stop by his place first. _ Shaun got the address from Caleb and sent it as well, trying to hide his concern. That area was far from Emon U campus, and not at all a place he’d want Caleb to live.

After a few minutes, Sherri arrived. Shaun opened the door for Caleb, letting him slip into the back. The car was spacious, not as big or ostentatious as a limo, but sumptuous, with clean leather seats and a near-permanent new car smell. Caleb buckled up as Shaun did.

Sherri turned to check them, eyeing Caleb from behind her thick spectacles. As she turned back around, she muttered, “Are you sure it’s alright to go into that area?”

Caleb tensed, muttering, “It is alright, you do not have to--”

“No, it’s fine, Sherri. We’ll be fine.” He sat taller, hand moving closer to Caleb’s. He took it. His hand was soft, and Shaun just now noticed how small it was.

The drive there wasn’t long. As soon as they arrived at the shabby, barely-lit apartment building, Caleb shed the jacket and said, “I will be quick,” hurrying out as he fumbled for his keys.

Shaun sighed. The place looked like it was falling apart. He pulled up his note-taking app, finding the newly emptied list he used for his partners.  _ New place to live _ became his first addition.

* * *

Caleb hurried through his things, dumping out his school backpack to quickly pack clothes, underwear, toothbrush, hairbrush, deodorant. He had not expected to feel quite so excited to spend the night, but that feeling was partially laced with dread. He had a good thing now. A  _ wonderful _ thing. A thing that could change his life for the better.

But that thing could leave him in an instant, his thoughts reminded him. Leave him to his shitty apartment and his student debt and his dimming hope and chances for his transition.

He stuffed some condoms in the bag last-minute. They were cheap, probably beyond expired, and definitely covered in dust. But Caleb put them in there, just in case.

He zipped it up after grabbing his phone charger and texting Allura (as much as he did not want to; he just had no one else) that he was spending the night with someone. Allura just sent a thumbs-up emoji in reply. He stuffed the phone into his pocket, locked his apartment door, and hurried back to the car.

_ Thank the gods, the car is still there. _

Caleb slid back in, setting the bag at his feet. “Sorry for the wait,” he mumbled as he put on the coat and buckled up again. (He was not  _ terribly _ cold, but the suit jacket felt comforting and smelled slightly of peppery cologne that made his heartbeat settle.)

“It’s not a problem,” Shaun said, quickly finding Caleb’s hand and giving it a squeeze. Caleb should not be feeling so happy so soon when this could be taken away so easily, but he squeezed in return and indulged himself in the happy thought of maybe lasting longer than Gilmore's typical plaything.

The area that they entered was far beyond the wealth that Caleb had ever seen before. The apartment buildings seemed to disappear into the night sky, the streets well lit and clear of most cars. Sherri pulled into a parking lot full of shimmering, expensive-looking vehicles.

“Thank you very much, Sherri,” Gilmore said as he got up.

“Don’t pull a muscle,” she retorted, and Gilmore laughed heartily.

“Good one,” he said, and Caleb quickly got out, watching Sherri drive away before following Gilmore to the apartment.

The doorman smiled and opened the door for them. (Caleb had always thought they were just a thing in movies and TV, blinking a little in surprise when he saw him.) The lobby was gorgeous, yellow-lit with fancy tile and red carpets and antique-looking furniture in pristine condition. Gilmore brought him across the lobby, greeting the lady at the front desk and the security guards, before he took a card from his wallet, scanned it against a small camera by the elevators, and pressed an up arrow button. The elevator arrived quickly, dinging softly as it opened. On the wall opposite the door was a floor-to-ceiling window, revealing a small plaza with lit greenery and stone benches. They went inside, and Gilmore said, “Watch this.” He pressed the highest button, and the doors slipped shut. He and Caleb both turned to watch as they ascended high above the other buildings, the city lights turning into upside-down neon stars.

Caleb smiled. “I have never been up this high,” he muttered.

“Glad your first time was this.”

Caleb looked up at Gilmore. He was staring at him with an unbearable softness in his eyes. His hand moved to Caleb’s cheek, cupping it as he moved in for a kiss.

His lips were surprisingly soft, the taste of champagne and chocolate still lingering on them. Caleb had not been kissed in so long, he had forgotten how much he had _missed_ it until he dropped his backpack so that both of his hands could press up against Gilmore’s chest.

The elevator dinged, and they broke up their kiss just long enough to get his bag and go through the opening doors. Caleb didn’t pay much attention as Gilmore got them into the apartment, turned on the lights, brought him down the hall. All he could think of was his  _ lips _ , his hands on his waist, his guiding grip, the _cologne_ , now stronger smelling, the beat of his heart and the pace of their breathing. 

Gilmore paused when they were down a hall, at what Caleb assumed to be the bedroom door. “Are you sure--”

Caleb interrupted with a breathless  _ bitte _ before Gilmore opened the door. Caleb’s bag fell once again as they kicked off their shoes and Caleb shucked off the coat, moving towards the bed. The trip was somewhat longer than Caleb expected, but he thought little of it, hands too busy fumbling with his shirt buttons.

Gilmore stopped him again. “Wait. Do you have a safeword?”

“Stoplight system?” Caleb muttered, just now noticing how quickly his breath had turned into panting.

“Any no-gos? Places I shouldn’t touch or pay attention to?”

Caleb paused. “My chest. And don't mention my face or voice.”

“Top or bottom? For you, I mean. I can do either, but I haven’t prepped.”

“I can be the bottom,” Caleb said. He was a bit used to it -- even in his previous fumbling trysts, he was the one receiving. He didn’t mind, though; his bottom dysphoria was minimal, miraculously.

“Alright. Any words you want to use for your body?”

No one had asked him that. Not even Molly, though they mostly avoided using anything distinctly feminine. “I don’t know.”

“Okay. I’ll just use masculine terms, but let me know if you feel uncomfortable, okay?” Shaun brought up his chin with one hand to make sure Caleb was looking at him. The touch made Caleb’s heart thrill with a new feeling of pleasure. 

Caleb could only nod, his breath and heart rate still quick.

Shaun smiled. “Alright.” His voice lowered, deepened, quieted to a vibrating tone that made Caleb shiver. He kissed Caleb again, less urgently but harder now, pressing his collarbone softly to guide him towards the bed. The touch made Caleb moan softly, surprisingly. He didn’t know this was a  _ thing _ for him, but by the gods, he felt so hair-trigger he thought any more contact could make him combust.

Caleb’s calves bumped into the bed, and his fingers returned to his shirt, undoing it. He almost apologized for the condition of his binder, stretched out and threadbare in places, but he stopped. Gilmore was busy taking off his own shirt, showing a soft, hair-covered chest that was graying in places. His skin was a gorgeous tan, and Caleb felt his shirt tumble off him as his hands stretched out to  _ touch. _ His skin was warm and soft, and his hands moved towards Caleb’s waist, then his ass to squeeze experimentally. Another moan escaped from Caleb’s lungs as Gilmore kissed his neck, hands lifting him up to sit on the bed.

“Can I take off your binder?” Gilmore whispered, lips tracing over Caleb’s burning skin.

Caleb sighed. He hated taking it off, but having badly bruised his ribs from his first romp with Mollymauk, he knew it was a terrible idea. His own fingers pulled it off, and he was grateful that Gilmore’s gaze didn’t linger on that area, his lips skipping over to his stomach as his hands went to his belt.

“Can I suck you off?” Gilmore asked. Another unexpected thing that Caleb liked to hear.

“ _ Ja _ ,” he said. He had received enough oral sex to know that he liked it, though the memories of it still felt distant and bittersweet.

Gilmore skillfully undid his belt, lips lingering above the waist of Caleb’s pants while his fingers handled the button, the zipper, and brought them and his boxers down. Without looking much at what lay between Caleb’s legs, Gilmore quickly brought his mouth against it, his tongue moving gently at first. Caleb moaned -- holy  _ fuck, _ how did he forget how  _ good _ this was.

Caleb’s legs went over Gilmore’s shoulders, and he quickly grabbed a throw pillow to place under his hips. “ _ Fuck _ ,” Caleb muttered, feeling the tight grip of Gilmore’s hands on his bare thighs. Gilmore’s tongue, for that of a gay cis guy, was  _ adept _ at making Caleb whimper. His hands, in need of something to grip, went to the duvet, clenching the silken fabric as his back arched. Gilmore’s tongue explored him, from top to hole, teasing at first but working him up. Caleb moaned, not noticing how loud he was, or how tight his thighs wrapped around Gilmore’s cheeks, and not caring. His words became a long string of  _ fuck, Gilmore, please, fuck, yes, gods, yes, right there, fuck yes, fuck me, fuck, fuck, fuck-- _

The tight grip of his orgasm came in sudden waves, leaving him thrashing a bit as he all but  _ screamed _ with its force. Once he was done, strung out and panting, Gilmore set him down, tossing aside the pillow as he came up to Caleb. “Can I kiss you?” he mumbled, voice low and deep enough to make Caleb inches from being horny again, and Caleb responded by pulling him in and letting him taste the cum on his lips.

Gilmore quickly rolled over, letting Caleb straddle his stomach a little as he undid his pants and took them off. Caleb turned to see his cock and  _ gods,  _ it was big, and Caleb  _ needed it _ . 

“Condoms?” Caleb asked.

“You sure? Don’t wanna break you during our first time.”

“ _ Please _ , sir--” Caleb said, kissing him needily.

“Nightstand, right behind you,” Gilmore said without pause, repositioning as Caleb opened the drawer and pulled one from the stack, checking the wrapper, the date, opening it.

Caleb got back on the bed and mumbled, “Let’s see if my muscle memory is as good as I think,” before putting the condom in his mouth, flipping it with his tongue just as Molly taught him, getting it into position. Before Gilmore could give him more than a confused look, Caleb got between his legs, took his cock in his hand, pulling the foreskin back a bit as he slid the condom on with his mouth.

Gilmore moaned, making a sound that made Caleb weak-kneed, and murmured, “You’ll have to teach me  _ that  _ trick.” Caleb smiled as he rose to kiss Gilmore, his neediness returning. He moaned softly as Gilmore’s hand went to his wet hole. “Can I make sure you’re able to take me?” he asked.

“ _ Bitte _ , give me anything,” Caleb muttered, and Gilmore obliged. They shifted a little, and Gilmore’s middle finger extended into Caleb, dragging out a tiny moan from him as he began to move it. One finger became two, then three as Caleb relaxed, pleasure building again in his gut. He began muttering in strings again, forgetting to breathe between words.  _ Fuck me Gilmore bitte please fuck me fuck me fuck fuck fuck. _

When Caleb began to twitch, Gilmore asked, “Position?”

“Any, please, fuck me--”

Gilmore moved Caleb to his hands and knees. “This okay?”

Caleb felt like he was about to explode. “Would it be okay if you were a little rough?” he asked before he could think to hesitate.

“I can oblige,” he said, lifting Caleb up to slide a pillow under his hips before pushing him down into the mattress, his other hand pumping his cock. “Want me to call you anything?”

“I kind of like being called a slut?”

“Alright.” Without another word, Gilmore slid slowly in, and Caleb forgot what words were. He felt like he was filled out completely. There were no more thoughts in his mind, no semblance of language, only sounds and feelings and  _ pleasure _ . Once he was firmly in, and the rhythm was established, Gilmore shifted. His grip became tight, his pressure on Caleb’s shoulder rough, his voice a guttural growl as the thrusting of his hips increased.

“Moan for me, slut,” he commanded, leaning in close to Caleb’s ear. “I want to hear your pleasure.”

Caleb obeyed with eagerness and sincerity.

His fucking became ruthless, making the bed creak and thud against the wall. He held onto Caleb’s hair at some point, the grip bringing a higher pitch out of Caleb. Gilmore’s name became a repeated chant, Caleb’s voice growing higher and louder. He begged. He moaned. He screamed and sobbed.

Nothing existed outside of his body, the bed, and Gilmore.

Caleb’s first orgasm came out of nowhere. The second was more of an aftershock following the first. At some point, Caleb lost count of them, just  feeling them shudder through him like a roaring train . At some point, Gilmore’s voice returned as he pressed up against Caleb, saying, “ _ Fuck yes, my good little slut, make me fucking cum. _ ” One sharp thrust, then two, and Gilmore moaned  _ loud _ against the back of Caleb’s head as he came. Caleb felt like he had melted as Gilmore rolled over, landing on the mattress, his weight making it shake.

_ By the gods, that was  _ divine, Caleb thought.

“Thank you,” Gilmore said.

Caleb hadn’t realized he was speaking out loud.

Once the endless chain of pleasure stopped, Caleb shifted to Gilmore's side, moving up to kiss him more. He needed to be with him like he needed air, water, and food. Gilmore’s skin was sunburn-warm and slightly sweaty, but he held Caleb close all the same, kissing him with a gentle force Caleb blissfully returned.

“You were wonderful,” Gilmore said, gazing at Caleb with starlit eyes. Then he chuckled. “Did I forget to take off your glasses?”

Caleb had not noticed, either. He took them off, only now feeling where they had been digging into his cheek. “No wonder I was seeing so clearly,” Caleb muttered.

Gilmore smiled and laughed, and Caleb forgot he had a heartbeat. His hand cupped Caleb’s cheek, thumb rubbing at the red pressure mark.

The look in his eyes felt too tender, and his touch was far too gentle to be safe.

Gilmore was either going to keep Caleb’s heart in his hands like the greatest treasure, or he was going to completely and utterly destroy it.

Caleb did not at all care. Losing it would be worth it if all he had was this.


End file.
